
Acetobromo-α-D-glucuronic acid methyl ester CAS 21085-72-3



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- Appearance: White powder
- Purity: 99. 0%min
- Stock: In stock
- Sample: Available
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Acetobromo-α-D-glucuronic acid methyl ester: The Complete Guide
- Item 1: Basic Info of Acetobromo-α-D-glucuronic acid methyl ester
- Item 2: What is Acetobromo-α-D-glucuronic acid methyl ester?
- Item 3: Acetobromo-α-D-glucuronic acid methyl ester Uses
- Item 4: The Manager has Something to Say
- Item 5: Preparation of Acetobromo-α-D-glucuronic acid methyl ester
- Item 6: Reference
- Item 7: Quality Control of Acetobromo-α-D-glucuronic acid methyl ester
- Item 8: Hot Sale Products
- Item 9: Get Acetobromo-α-D-glucuronic acid methyl ester Quotation
Acetobromo-α-D-glucuronic acid methyl ester for Sale
Basic Info of Acetobromo-α-D-glucuronic acid methyl ester
Chemical Name: | Acetobromo-α-D-glucuronic acid methyl ester |
Other Name: | ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER; 1-Bromo-2,3,4-tri-O-acetyl-α-D-glucuronic Acid Methyl Ester; 1-Bromo-1-deoxy-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester; Acetyl bromide- α- Methyl D-glucuronate |
CAS: | 21085-72-3 |
EINECS: | 244-203-4 |
Type: | Pharmaceutical intermediate |
Molecular Formula: | C13H17BrO9 |
Molecular Weight: | 397.17 |
Melting point | 80-110 °C(lit.) |
Boiling point | 388.6±42.0 °C(Predicted) |
density | 1.52 |
storage temp. | Inert atmosphere,Store in freezer, under -20°C |
solubility | Acetonitrile (Slightly), Chloroform (Slightly, Heated, Sonicated), Dichlorometha |
form | Crystalline Powder or Solid |
color | White to gray |
Stability: | Moisture and Temperature Sensitive |
Brand Name: | Zhishang Chemical |
Provide: | Acetobromo-α-D-glucuronic acid methyl ester MSDS; Acetobromo-α-D-glucuronic acid methyl ester COA |
What is Acetobromo-α-D-glucuronic acid methyl ester?
Alpha-D-glucuronic acid methyl ester, also known as acetyl bromide-α-D-glucuronic acid methyl ester, can be prepared from D-glucuronic acid methyl ester by using D-glucuronide as raw material, and then acetylated. Obtain 1,2,3,4-tetra-O-acetyl-D-glucuronic acid methyl ester, and finally brominate to obtain A-D-glucuronic acid methyl ester.
Acetobromo-α-D-glucuronic acid methyl ester Uses
- Acetobromo-α-D-glucuronic acid methyl ester was used to synthesize hmr1098-s-methyl glucuronate, which is a new K-ATP blocker and can be used as a drug to prevent sudden cardiac death.
- Acetobromo-α-D-glucuronic acid methyl ester (cas 21085-72-3) is a useful compound, which can be used to prepare fluorescent probes for human heparanase.
- Acetobromo-α-D-glucuronic acid methyl ester is used to synthesize camptothecin water-soluble glucosidic acid derivatives for cancer prodrug monotherapy and antibody directed enzyme prodrug therapy (ADEPT).
- Acetyl bromide- α- Methyl D-glucuronate is used to synthesize the glucuronic acid prodrug compound of tofatinib, a Janus kinase (JAK) inhibitor, which can be β- The cleavage of glucuronidases, such as those produced by the gastrointestinal microbiome, increases the level of tofatinib at the site of gastrointestinal inflammation and limits the systemic exposure of tofatinib in the treatment of local inflammatory diseases.
The Manager has Something to Say

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Preparation of Acetobromo-α-D-glucuronic acid methyl ester
- Synthesis of D-glucuronic acid methyl ester. It can be represented by the following reaction formula:
The specific preparation steps are as follows: D-glucurolactone (1) (17.6 g, 0.1 mol) was dissolved in 200 ml of methanol, and cooled to 0 °C. NaOH (100 mg) was added and stirred for 2 hours. The reaction was concentrated to dryness to give methyl D-glucuronate (2) as a white solid (yield 20.8 g, 100% yield). - Synthesis of methyl 1,2,3,4-tetra-O-acetyl-D-glucuronic acid. It can be represented by the following reaction formula:
The specific preparation steps are as follows: D-glucuronic acid methyl ester (2) (20.8g, 0.1mol) was dissolved in pyridine (45ml) and cooled to below 5°C, then acetic anhydride (54mL, 0.6mol) was added dropwise to maintain stability Not exceeding 10°C, then stirring at room temperature for 3 hours. The reaction was concentrated to dryness and dissolved in 300 mL of dichloromethane, then the organic phase was washed three times with water, dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated to dryness, and 100 mL of methanol was added to precipitate a solid. The solid was filtered to give methyl 1,2,3,4-tetra-O-acetyl-D-glucuronic acid (3) (yield 24.4 g, 65% yield). - Synthesis of acetyl bromide-α-D-glucurone acid methyl ester. It can be represented by the following reaction formula:
The specific preparation steps are as follows: 1,2,3,4-tetra-O-acetyl-D-glucuronic acid methyl ester (3) (15.0 g, 4 mmol) was added to an acetic acid solution of hydrogen bromide (hydrogen bromide The mass percentage of 33%) (60 mL) was kept stable at no more than 10 °C, and then the temperature was naturally raised to room temperature and stirred for 2 hours. The reaction was concentrated to dryness and dissolved with 100 mL of ethyl acetate, then the organic phase was washed three times with aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated to dryness, and 50 mL of petroleum ether was added to precipitate a solid. The solid was filtered to obtain A-D-glucuronic acid methyl ester (4) (yield 14.3 g, yield 90%).
To the commercially available D-glucuronic acid-6,3-lactone compound (6) (48.6 g, 276 mmol) was added anhydrous methanol (500 mL) and metallic Na (200 mg) at 0°C. The mixture was stirred under N2 for 5 hours. The solution was treated with IR-120(Ir) resin until pH3. The solvent was removed in vacuo after filtration to provide a yellow gum. The residue was partially dissolved in Ac2O (100 mL) and a solution of HClO4 (0.1 mL) in Ac2O (1 mL) was added dropwise to the reaction mixture at a rate such that the solution did not exceed 40°C. The reaction mixture was then stirred at rt under N2 overnight. The product was then dissolved in ethyl acetate, washed with 1N HCl, H2O and brine, and the organic phase was dried over Na2SO4. The solvent was removed in vacuo to afford the per-O-acetate intermediate compound (5) (96.5 g, 93%) as a white gum with alpha/beta ratio 75:25.
To the per-O-acetate compound (5) (7.73 g, 20.54 mmol) obtained above was added dropwise 45% HBr/acetic acid (25 mL) at 0°C under N2. The round bottom flask was placed in a desiccator and stirred at 4°C for 48 hours. The mixture was diluted with ethyl acetate (100 mL) and poured onto ice (50 g). The solution was washed with saturated aq. NaHCO3 (50 mL), brine (50 mL), H2O (100 mL), the organic phase was dried over Na2SO4, filtered and the solvent removed in vacuo. The product was purified by flash chromatography (2:1 hexanes/ethyl acetate) to provide glucuronyl bromide (3) (3.50 g, 43%) as a pink gum.
Reference
- Acetobromo-alpha-D-glucuronic acid methyl ester – PubChem
- CN201810068438.1 Substrate for detecting β-D-glucuronidase and preparation method and kit thereof
Quality Control of Acetobromo-α-D-glucuronic acid methyl ester

